Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes

被引:84
|
作者
DiMauro, EF [1 ]
Kozlowski, MC [1 ]
机构
[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol016535u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A set of modular bifunctional salen catalysts which contain Lewis acid and Lewis base activating groups is described. These groups can be altered independently to control nucleophilic and electrophilic activation of the reacting substrates, These salen-derived catalysts show enhanced reactivity in the addition of diethylzinc to aldehydes with respect to most other salen, amino alcohol, and diamine derived catalysts and reactivity comparable to that of Ti complexes of bis-sulfonamides and diols.
引用
收藏
页码:3053 / 3056
页数:4
相关论文
共 50 条
  • [1] Enantioselective diethylzinc addition to aldehydes using azetidine-derived chiral catalysts
    Hermsen, PJ
    Cremers, JGO
    Thijs, L
    Zwanenburg, B
    TETRAHEDRON LETTERS, 2001, 42 (25) : 4243 - 4245
  • [2] Aziridino alcohols as catalysts for the enantioselective addition of diethylzinc to aldehydes
    Tanner, D
    Korno, HT
    Guijarro, D
    Andersson, PG
    TETRAHEDRON, 1998, 54 (47) : 14213 - 14232
  • [3] CHIRAL PIPERAZINES AS CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
    FUJI, K
    TANAKA, K
    MIYAMOTO, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (09) : 1557 - 1561
  • [4] The synthesis of new oxazoline-containing bifunctional catalysts and their application in the addition of diethylzinc to aldehydes
    Coeffard, Vincent
    Mueller-Bunz, Helge
    Guiry, Patrick J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (08) : 1723 - 1734
  • [5] Enantioselective addition of diethylzinc to aromatic aldehydes with aminophenol as catalysts
    Li, XS
    Shen, ZX
    Ge, JF
    Zhang, YW
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (04) : 387 - 389
  • [6] CHIRAL OXAZABOROLIDINES AS CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
    JOSHI, NN
    SREBNIK, M
    BROWN, HC
    TETRAHEDRON LETTERS, 1989, 30 (41) : 5551 - 5554
  • [7] Aziridine sulfides and disulfides as catalysts for the enantioselective addition of diethylzinc to aldehydes
    Braga, AL
    Milani, P
    Paixao, MW
    Zeni, G
    Rodrigues, OED
    Alves, EF
    CHEMICAL COMMUNICATIONS, 2004, (21) : 2488 - 2489
  • [8] Chiral zinc amides as the catalysts for the enantioselective addition of diethylzinc to aldehydes
    Prasad, KRK
    Joshi, NN
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11): : 3770 - 3771
  • [9] Salicylaldehyde based oxazolidines as catalysts for the asymmetric addition of diethylzinc to aldehydes
    Parrott, Raleigh W., II
    Hamaker, Christopher G.
    Hitchcock, Shawn R.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (03) : 873 - 878
  • [10] Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes
    Yang, XW
    Shen, JH
    Da, CS
    Wang, R
    Choi, MCK
    Yang, LW
    Wong, KY
    TETRAHEDRON-ASYMMETRY, 1999, 10 (01) : 133 - 138